2-Thiopheneethanol → 1-Benzhydryl-3-(2-(thiophen-2-yl)ethoxy)azetidine

HRID 633937

Reaktionsgleichung

Reaktionsgleichung von HRID 633937
CS([O:5][CH:6]1[CH2:9][N:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1)(=O)=O.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[CH2:28][CH2:29]O>>[CH:10]([N:8]1[CH2:9][CH:6]([O:5][CH2:29][CH2:28][C:24]2[S:23][CH:27]=[CH:26][CH:25]=2)[CH2:7]1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

3

Edukt 2

HCID 794002-ThiopheneethanolHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Produkt 1

HCID 671545391-Benzhydryl-3-(2-(thiophen-2-yl)ethoxy)azetidine

Versuchsvorschrift

A solution of 1-benzhydrylazetidin-3-yl methanesulfonate (324 mg, 1.0 mmol) in thiophene ethanol (2.3 mL, 20.4 mmol) was stirred under microwave irradiations (100 W) at 110° C. for 30 minutes. The reaction mixture was then partitioned between dichloromethane (20 mL) and a solution of sodium hydroxyde (1N, 10 mL). The aqueous layer was separated and extracted with dichloromethane (2×10 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel, using petroleum ether/ethyl acetate (85:15) as eluent. The title product was obtained as a yellow solid (210 mg, 59%).

Aufarbeitung

  1. customThe reaction mixture was then partitioned between dichloromethane (20 mL)
  2. customThe aqueous layer was separated
  3. extractionextracted with dichloromethane (2×10 mL)
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4098e36ff5ce4c21b526142e00e46b15
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321769B2

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